FlySketch
Victor, over at our sister-site DownloadSquad, spotted FlySketch, which brings one of my favorite high school pastimes, doodling, to your Mac OS X desktop. The program runs $24.95, or $39.95 when bundled with VoodooPad.
FlySketch is like a screen-capture tool that lets you doodle on the images as you take them: "When called upon, FlySketch will show its main drawing window above all other windows in the system. Change the transparency of the canvas, and you can trace, draw over, highlight, and capture just about anything that shows up behind FlySketch." You can then email the resulting images, drop them into chat with a friend, or incorporate them into some documentation you are slapping together for the company's IT department. There's a free demo. Check it out.